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CAS No. : | 885278-42-2 | MDL No. : | MFCD07371573 |
Formula : | C9H7BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 255.07 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.07 |
TPSA : | 54.98 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.13 cm/s |
Log Po/w (iLOGP) : | 1.8 |
Log Po/w (XLOGP3) : | 2.43 |
Log Po/w (WLOGP) : | 2.11 |
Log Po/w (MLOGP) : | 1.76 |
Log Po/w (SILICOS-IT) : | 2.51 |
Consensus Log Po/w : | 2.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.3 |
Solubility : | 0.129 mg/ml ; 0.000506 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.151 mg/ml ; 0.000592 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.84 |
Solubility : | 0.0365 mg/ml ; 0.000143 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium carbonate In acetonitrile at 20℃; for 15 h; | Intermediate Preparation 4 IB; Methyl 6-bromo- 1 -methyl- lH-indazole-3 -carboxylate; To a mixture of methyl 6-bromo- lH-indazole-3 -carboxylate (0.50 g, 1.96 mmol) and potassium carbonate (1.28 g, 9.29 mmol) in acetonitrile (15 mL) is added methyl iodide (1.31 g, 9.29 mmol) at room temperature. The reaction mixture is stirred at room temperature for 15 h. Remove the solvent under vacuum, dilute with water, and extract with ethyl acetate (3x 10 mL). The combined organics are dried over sodium sulfate and concentrated under reduced pressure. The crude is purified by flash chromatography eluting with 8:2 hexane/ethyl acetate to give 0.35 g (70percent) of the title compound as an off white solid. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 4.14 (s, 3H), 7.42 (dd, J= 8.4, 1.2 Hz, IH), 7.66 (s, IH), 8.08 (d, J= 8.8 Hz, IH). |
70% | With potassium carbonate In acetonitrile at 20℃; for 15 h; | To a mixture of compound H3 (7 g, 27.45 mmol) and potassium carbonate (45 g, 137.25 mmol) in 200 mL of CH3CN was added CH3I (19.60 g, 138 mmol) at room temperature The reaction mixture was stirred at room temperature for 15 h. Concentrated under reduced pressure, diluted with water, and extracted with EtOAc (10 mL*3). The combined organics were dried over Na2SO4 and concentrated under reduced pressure The crude residue is purified by flash chromatography (eluent: PE/EA = 4 1) to give 4 9 g of compound H4 as a yellow solid (Yield: 70percent). |
0.75 g | With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 0 - 25℃; for 16 h; | To a solution of methyl 6-bromo-1H-indazole-3-carboxylate (1.3 gm) in Acetonitrile (20 ml) and DMF (3 ml) was added Potassium carbonate (3.52 gm) at ambient temperature. Then Methyl iodide (1.27 ml) was added to the reaction mixture at 0 °C. Reaction mixture was stirred at room temperature for 16 h. Progress of reaction was monitored by TLC. After completion of reaction, reaction mixture was diluted with water (80 ml) and followed by extraction with ethyl acetate (50 ml x 3). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (eluting in 5-30percent ethyl acetate in heptane as a mobile phase) to afford of title compound (0.750 g). HPLC/MS (method 1): Rt : 1.876 min; MS: m / z = 269.10 (M+1).1H NMR (300 MHz, Chloroform-d) δ 8.11 (d, J = 8.6 Hz, 1H), 7.68 (s, 1H), 7.44 (dd, J = 8.6, 1.3 Hz, 1H), 7.28 (s, 1H), 4.16 (s, 3H), 4.06 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | at 90℃; for 4 h; | To a suspension of 6-bromo-1H-indazole-3-carboxylic acid (3.00 g, 12 mmol) in methanol (50 mL, 1 mol) was added Sulfuric acid (1.50 mL, 28 mmol), and the mixture was heated to 90 °C for 4 hours. After cooling to rt, the mixture was diluted with 200 mL EtOAc, and washed with 150 mL sat. NaHC0 2 (aq) and 150 mL brine. The organic extracts were dried (Na 2 S0 4 ) and concentrated in vacuo to provide 2.42 g (76percent) of pure 6-bromo-lH-indazole-3-carboxylic acid methyl ester as a yellow solid. This material was diluted in tetrahydrofuran (50 mL), cooled to 0 °C, then sodium hydride (0.417 g, 10.4 mmol) was added. The mixture was stirred at 0 °C for 30 minutes, then [β-(trimethylsilyl)ethoxy]methyl chloride (1.85 mL, 10.4 mmol) was added dropwise. The mixture was allowed to slowly warm to room temperature over 90 minutes, then MeOH was added to quench excess hydride, and the mixture was concentrated in vacuo. The residue was diluted with 200 mL EtOAc, then washed with 200 mL brine. The aqueous layer was further extracted with 50 mL EtOAc, then the combined organic extracts were dried (Na2SO4 ) and concentrated in vacuo. Purification by CombiFlash (40 g column; load with CH2Cl2 ; 100:0 to 50:50 heptane:EtOAc over 30 minutes) provided 3.22 g (88percent) of the title compound as a yellow oil. |
51% | for 22 h; Reflux | Catalytical amount of con. H2S04 was added to a stirred solution of 6- bromoindazole-3-carboxylic acid (lg) in MeOH. The reaction mixture was heated to reflux for 22h. After completion of reaction (monitored by LCMS) the solvent was removed by rotovapor and the residue was dissolved in dichloromethane (25 mL). The organic layer was washed successively with saturated solution of NaHC03 and brine followed by drying over anhydrous Na2S04. The solvent was removed by rotovapor and the residue was purified by flash chromatography to yield the desired ester (18-1) in 51percent yield. |
35% | Stage #1: at 0℃; Reflux Stage #2: With sodium hydrogencarbonate In water |
To a solution of compound H2 (20 g, 84 mmol) in 200 mL of dry MeOH was added dropwise cone. H2SO4 (15.4 g, 168 mmol) at 0~5°C . The resulting mixture was refluxed overnight. The reaction mixture was filtrated, evaporated, and poured into water (50 mL). The solution was adjusted to pH = 7 with a saturated NaHCO3 aqueous solution, extracted with ether (50*3 ml), dried over MgSO4, concentrated and purified by flash chromatography on silica gel (eluent: PE/EA = 1/1) to give 7.1 g of compound H3 as a yellow solid (yield: 35percent). |
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